Five Days in New York: How To Do Everything

So you’ve booked your flights and hotel to the Big Apple and it’s a little while until you go, plenty of time to plan. You start looking online for ideas and inspiration for where to go and what to see; it’s all a bit overwhelming and you tell yourself you’ll come back to it. You buy a guidebook, thicker than you thought, and start trying to narrow down what to do. Again, it’s so full of ideas you don’t know whether to start at the back or the front. Have no fear. I had five days in New York and I have been through the process for you; here’s how I did it all.

We went in June last year, when it’s warm but not too hot. You have a few choices for how to get to the city from the airport (we landed at JFK) and decided that the subway was certainly the cheapest option but not something to take on when jetlagged. A taxi would be too expensive so we opted to take the NYC Airporter; basically a bus direct from the airport to Grand Central station which we booked in advance. Stress free, and you get great views of Manhattan on the way in. Below the places we visited are in bold, places we ate are in italics.

An introduction to New York if I may. Avenues go up and down, numbered from left to right. Streets go across the city, numbered from the bottom up. It gets a bit confusing down the bottom end where they start using fruits to name the streets rather than numbers but other than that it’s so logical you’ll be pushed to get lost. I saw many less classic American cars than I was expecting and the whole city seemed to be working on itself almost everywhere: repaving paths, tarmacking the roads, we even accidentally walked onto a film set (and were swiftly asked to leave) and there really are that many Starbucks.

Day 1:

The bus takes you right outside the entrance to Grand Central Station so we thought we might as well go in, see the famous clock and ceiling, then go to the hotel. I was expecting the clock to be somewhat larger than it was, you’ll think you’ve missed it, but the ceiling was wonderful. Be aware that there are an awful lot of people wearing backpacks absent mindedly wandering along looking at the ceiling; a collision is almost inevitable.
We unloaded our things at the hotel, a few streets down from Central Park, and headed straight back out to see everything.
First stop was a wander up 5th Avenue towards Central Park then a sit down on one of the classic benches along a tree lined path to eat a pretzel and watch the world go by. Further wandering around the park brought us to some jazz musicians and The Boathouse and the Bethesda Fountain. Unfortunately we felt somewhat underdressed to attempt to get a table in The Boathouse so instead headed back out of the park over the opposite side and headed for Times Square.
It turns out that Times Square is in fact not a square at all but more of a larger gap than normal between the avenues where every street, avenue and building is covered in lights. It’s all very mesmerising, and somewhat disorientating but sitting down on the famous red steps is a great place to take it all in. I learnt very quickly to put on my ‘serious’ face when walking in any of the tourist spots in the city. Look focussed and no one will bother you or try to sell you anything. Maybe I used my angry face, I’m not sure, but either way I didn’t get bothered much.

After Times Square we were getting a little hungry, it was about 6pm at this point and we found a brewpub nearby at 127W 43rd Street between 6th and 7th Avenue called Heartland Brewery. Our first taste of American beer, food and service all occurred in the same place. We ordered the beer taster; eight different beers, some of them regular brews and some limited edition before deciding that actually we quite liked sitting down and therefore would quite like to have some dinner. The food here was exactly what we were after; properly indulgent and absolutely delicious. We shared beer battered onion rings and southern fried gherkins (with ranch dressing) to start and followed this with a burger and waffle fries each. This was the best burger I have ever had, I have tried burgers here since I got back but nothing has come close to this. Not too big so you can actually eat it like a proper burger, juicy and flavoursome with Swiss cheese and fried onions. It was almost disgustingly good.

You need to be aware before you go about service charge added to all the bills in NYC, it’s just one of those things, but as the service was always excellent I didn’t ever mind paying it. If you want to stay away from it, get street food (not cart food!), fast food or something from a supermarket. But be aware you might be missing something amazing…or discovering something equally as good.
After this, we needed to walk it off, we headed back to 5th Avenue to go in the opposite direction to earlier. We actually ended up by New York Library, but it was closed, and by this time we were feeling pretty tired so headed back to the hotel for an early night. Unbeknownst to me my OH had had a rather stressful day, he was carrying a ring around in his pocket the whole day you see, and hadn’t yet found some time where we weren’t walking, eating, or surrounded by selfie sticks to be able to ask an important question. So, back at the hotel, Manhattan glistening outside the window, (both of us extremely tired) he got down on one knee and I said yes.

Day 2:

Very much refreshed after an early night and a lie in to get over the jetlag we grabbed a takeaway coffee and bagel from the hotel and wandered over to the top of the High Line at W30th St between 10th and 11th Avenue, taking in the Hudson River as we walked down to find it. Every part of the High Line has something different on it; gardens, sculptures, water features there was even a café come market halfway down. It’s a great way to see the city, and as we got there early morning it was pretty quiet. The High Line spits you off down in The Meatpacking District and from here we walked all the way down, taking in Greenwich on the way and another coffee to Wall Street and the Financial District for a wander round. Trying to get a picture of the Charging Bull was pretty much impossible because of the many other tourists trying to do the same thing.

It had been raining a little but it was drying up so we went over to see the Reflecting Pools at the September 11 Memorial. We didn’t stop to go to the museum but just being around the pools was moving. Of all the places in New York I didn’t expect to see people taking selfies it was here, but I was unpleasantly surprised that they were. It’s quite a place to be. Being around this area also meant we got to see the brand new One World Trade Centre building which had just opened a few days before.

It was getting towards lunchtime now so we headed away from the south of Manhattan and wandered through China Town. An amazing mixture of colours and smells we went all the way through and found ourselves in Little Italy. And then we had to try and choose somewhere for lunch. We settled somewhere that was probably a tourist spot but the portions were generous and the food very good (and reasonable at two courses for $18 or something) so we filled up on carbs before an afternoon of more walking.
By this point I was very pleased with my choice of footwear, I can’t imagine how far we had already walked and there was plenty more to come. We headed over to Soho and Noho which were great; wider streets, lots of independent shops and little pop up markets in every nook and cranny.

We ended up in Chelsea and found a great space which looked to be home to a permanent market where the stallholders could change, or stay, with hot pizzas, cakes, juices, beers and all sorts. I tried a Bruffin; a brioche muffin and deliciously savoury. Not the culinary highlight of my trip but worth a go. We then headed to the more ‘formal’ Chelsea Market which was amazing. I didn’t know where to look first, the food and drink on offer was mind boggling and I actually ended up with a green tea lemonade. This is definitely worth a visit, you could stay there all day eating everything.

5th and 6th Avenues seemed to be where we always ended up so we headed down to the Flat Iron building and sat on a bench in the sun watching the city go by. We liked sitting, very much, by this point and as we headed back to our hotel along 5th we spotted the Belgian Beer Cafe where we stopped to refresh ourselves. We headed back, got changed and headed for the ‘famous’ Ellen’s Diner.
Everyone who we spoke to before we went mentioned Ellen’s Diner. We knew we would have to queue, we knew there was singing and we knew the food was probably not going to be the best in the city. We weren’t prepared for how much fun it was going to be. The whole restaurant is set up around a central ‘catwalk’ (but much thinner) where the waiting staff sing songs from Broadway and film. It was surprisingly unobtrusive but captivating; you could carry on your conversation no problem but also turn around and take in what was going on around you. I had a burger, again I know, which wasn’t as good as the night before but still better than anything you can get here!
As the diner is in Broadway we had a look around Times Square and Broadway again, but this time it was night and you can see the lights even more. We sat on the red steps overlooking the hustle and bustle before heading to, probably, New York’s most famous landmark of all.

The Empire State Building looks better further away. When you’re up next to it it’s so big you can’t really take it all in. We arrived to go up after 10pm and this was the best idea ever. We had to wait basically no time at all, the time was spent wandering through the queuing system and then a brief wait for the lift right up to the 86th floor. I knew the view would be great but I was pretty staggered by it; it was incredible. Times Square lets out so much light it’s almost daytime over there, Central Park is a huge, dark rectangle dividing either side covered with lights and you can’t see the stars no matter how hard you look. We then went up to the 102nd floor, which isn’t open air, and I have to say the view was pretty much the same! I couldn’t really see any difference but we would have regretted it if we hadn’t done it. And, in case you didn’t know, on Fridays and Saturdays at night they play jazz at the top.

Day 3:

You can’t go to New York and not take a ride in a yellow cab. I heard they were notoriously difficult to hail but I had no problem getting one the next morning from just outside The Waldorf Astoria (we tried to walk but after the day before our legs could do with a break) and we got a ride down to City Hall.

After a quick wander around and through a City Hall Park we walked over to cross the Brooklyn Bridge. Again, we were early in the morning so it was quite quiet to enjoy the views of Manhattan. We walked over to meet some friends and grabbed some breakfast in a local diner where they served anything you wanted, even if the constituent ingredients aren’t even on the menu. A fried egg and sausage muffin with unlimited coffee; sustenance for the day.

We took the subway (luckily our friend understood what was going on) over to the Brooklyn Brewery. To go in for a tour of the brewery is free, you just need to buy beer tokens and then try many beers before being shown round. It was really relaxed, and therefore very enjoyable and being in Brooklyn is like a breath of fresh air as there aren’t really any tall buildings and things are a bit more spread out. We had fantastic weather so wandered over to Williamsburg and visited Shmorgasburg which is a huge food and craft market with the East River and Manhattan as your backdrop; not sure there’s many places better than this for a market. Again, the variety was immense and the prices much cheaper than those at the markets over the river. I very much enjoyed a maple lemonade, chicken Caesar burger and matcha doughnut.
From here we then headed back over to the city over the Williamsburg Bridge (longest bridge I have ever walked over, it never seemed to end!) and ended up on the Lower East Side. We stopped in a local bar, The Boilermaker for some cocktails, and then another bar for more cocktails, before ending up at Mexican restaurant Dos Caminos. They know how to do guacamole. Over came a huge bowl, absolutely full of proper guac, a whole load of tortillas and three different chilli salsas. It turns out, they keep bringing tortillas until you run out of dips. Amazing. I then had pork tacos which were SO much better than anything I’ve had over here; soft tacos, full of spiced pork and fresh salsa. We were pretty full by this point but I managed to find room for some salted caramel cheesecake.

Day 4:

We had done plenty of the ‘tourist’ bits by this time so the last two days were available for relaxing and a slower pace. If you’re feeling up to it, you could use this day to go to Staten Island or The Statue of Liberty, but we were knackered! After leaving the hotel, we headed over to 8th Avenue and walked up towards Central Park, along the road and found a very small shop in a little alcove amongst all the residential buildings where we grabbed a coffee and the best blueberry muffin ever. There was a little bench outside to sit in the sun and have our breakfast.

We carried on walking and headed for the Guggenheim, it was such a nice day we decided not to go in, so instead turned around and headed into Central Park to overlook the Jacqueline Kennedy Reservoir. We then meandered down and ended up at the only roundabout in the city and then took Broadway down to Chelsea where we had lunch at The Forager.

The Forager is a great deli and restaurant, luckily we had booked a table for late lunch with our friends, as it was so busy. I had an amazing hot smoked salmon salad with lentils and a poached egg on rye and delicious unsweetened iced tea. Everyone’s food looked so good, it was in a great location and I wanted to buy everything in the deli!
After a wander around, and a stop off for a cocktail, we ended up at The Chester Biergarten a German outside bar where we were able to watch people desperately try to park their cars on the street while enjoying some great beers and waffle fries.
Then we headed to Penn Station to say goodbye to our friends, by which time it was dusk so we found a classic pizza place selling the huge slices (yes, they taste as good as they look), went past Radio City and The Rockerfeller to see them lit up at night before ending back in Times Square for a slice of classic cheesecake; it would be rude not to.

Day 5:

As this was our last day we had our bags with us so we weren’t going to go far (by bag, I mean very lightly packed back pack) so after breakfast at a diner we headed over to the Library, which was open this time, so we could look inside. It was a welcome bit of cool and calm after which we headed to The Chrysler Building, which we had seen from a distance so many times, but wanted to go and see it ‘up close’. We then went back through Grand Central Station to go to The Whispering Wall. It’s true that you can hear a whispered conversation corner to corner, above the throng going on around you, thanks to the special layout of the walls.

Grand Central Station actually has a market inside it, full of pastries, spices, sandwiches and the like. I thought it was a great place for a market, pick up everything you need on your way to or from somewhere.
We spent the early afternoon at Bryant Park, right next to the Grace Building, watching a mass yoga gathering and congratulating ourselves on doing everything we had wanted to see and do. Before we knew it we were back on the Airporter heading back to JFK for the flight home.
Of all the time we spent in New York we spent as much of it as possible outside. We saw MoMA, Macy’s, Bloomingdales and plenty of the other well-known establishments as we were wandering around and taking in the hustle and bustle. If you go, you need to be prepared to walk as it’s certainly the best way to see everything. If you only take a few pieces of ‘must-see’ from this, my top tips would be: The High Line, The Empire State (at night) and Chelsea and the Meatpacking district. And Brooklyn.
I would like to go again in the Spring to see the city in bloom and also in the autumn to visit the museums in between the rain showers. I ate more eggs in New York than I have probably eaten in my life, they come with everything, and I came back with a great appreciation for filter coffee. I ate and drank everything I could and had a fantastic time. Although I only spent five days there I feel like I could go back tomorrow, be dropped off anywhere, and know (almost) exactly where I was. Because you’ve seen it on screen so many times it almost feels like a home from home. I loved it and I can’t wait to go again.

Caroline, what a great post! You sure packed a lot of fun into a few days! I live just outside Washington D.C. but have only been to NYC a handful of times. I should plan a few days and really do it right, the way you did. Thanks so much for your tips and suggestions! : )

Love NYC! I used to commute in to work for a decade, and really enjoyed it. Sounds like you did and saw a lot! Still more to do and see, though, so you’ll have to schedule another trip. 🙂 Fun read — thanks.

Wow, Caroline, you didn’t waste a minute! I love NYC and there’s something new to discover every time you visit. Sounds like you had some great food, too! Loving that smoked salmon salad!
So nice to find your beautiful blog. Thanks for the visit 🙂